


In Your Hands

by Anonymous



Series: Adventures in Jack's sexual awakening [1]
Category: Supernatural
Genre: Hand Jobs, M/M, Masturbation, Mildly Dubious Consent, Oblivious Jack, Teaching
Language: English
Status: Completed
Published: 2020-01-27
Updated: 2020-01-27
Packaged: 2021-02-27 14:42:16
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,574
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22438927
Author URL: https://archiveofourown.org/
Summary: Jack wants to know about sex, and Dean indirectly gets him horny. Only makes sense that Dean's the one to take care of the problem then, right?
Relationships: Jack Kline/Dean Winchester, mentions of Dean Winchester/Castiel
Series: Adventures in Jack's sexual awakening [1]
Series URL: https://archiveofourown.org/series/1657693
Comments: 14
Kudos: 90
Collections: Supernatural Anon Kink Meme





	In Your Hands

**Author's Note:**

> Written for [this](https://spnkink-meme.livejournal.com/156628.html?replyto=47449556) prompt.
> 
> This is a Jack/Dean fic first and foremost!! There is a vague hint of Dean/Cas but it's not the main focus in this story.  
> Might be considered dub-con to some? Dean is under the influence and Jack is kind of oblivious to sex, but they both want this and it's consensual. The tag is there because rather safe than sorry!

It had started innocently enough. Jack had asked him about sex, so he had started by referring him to Reddit, figured the kid could ask around there and figure things out on his own. But that only led to more questions. Of course, the kid had to go and click all the links, apparently landing on one of the more nsfw subreddits. Dean should've seen this coming a mile away.

Next thing he knew, Jack was knocking on his door, face flushed red, not like he was embarrassed or anything, more like... "I feel hot," Jack had said, with an awkward downwards glance to the tenting in his pants. Jesus Christ. Dean had given him an earful, told him to go jerk off and sent him on his way with a box of tissues and some lube. He thought that was it, that the kid would tug one out and be done, have his sexual awakening, all that. But no, apparently nephilims were fucking oblivious to how the human body functioned, so later that night, there was once again a knock on Dean's door.

"What?" he called out gruffly from where he sat on the bed, back against the wall, book folded open in his lap.

Jack opened the door, not waiting for Dean to tell him to come in, his face still flush all the way from his cheeks to his neck, and an obvious erection straining against his pants.

Dean held up a hand in a half shrug. Apparently entering people's rooms uninvited ran in the angel gene pool.

"I don't know what to do?" Jack said, hand trembling on the doorknob, a scrunched up tissue and the bottle of lube held tightly in his other hand.

Dean swallowed. Shit. If it wasn't for the half of bottle of whiskey he'd already downed in an attempt to drown out the misery that was talking about sex and porn with Jack of all people, he might've gone about this differently. Maybe would've told him to take a cold shower, and to _never talk to him about this again_. As it was, the alcohol clouded his mind, and Jack looked a hell of a lot like Cas, so. Sometimes, things just happen.

Dean let out something between a sigh and a grunt and ushered Jack over with a wave of his finger, then slid his legs down to sit on the edge of the bed.

"Come here. Close the door." He patted a hand on the empty space next to him on the bed.

Thank fuck for alcohol. And library seminars. Sam wouldn't be home until much later, if Dean was going by past experiences. It was just the two of them home. It was fine. Jack needed someone to guide him through this, just like he'd needed someone to show him how to work the microwave or how to send a text. This wasn't much different. Not really.

Jack sat down on the edge of the bed, visibly uncomfortable at the strain over his crotch.

"Take off your pants." It was a simple command, and Jack followed blindly, pushing down both his pants and boxers to his ankles in one swift move, his skinny hips lifting up from the bed momentarily, making his dick bounce a little as it caught on the hem of his boxers.

Fuck, that was kind of hot, and birthed all kinds of thoughts in Dean's mind. He clenched his jaw.

"Okay, okay," Dean said and licked his lips, eyes tracing Jack's beautiful little cock, all red and hard.

"What do I do? Will you help me? You're good at this, right?" Jack's eyes were big and pleading, a small hopeful smile lingered on his lips.

Dean sucked in a breath. The kid _was asking_ for it. There was no harm in showing him how it was done, right? Then maybe he would get some peace and quiet later so he could turn back to his book. He pressed his lips together into a thin line.

"Yeah, yeah okay."

Dean rubbed his hands over his own thighs, trying to distract himself from the blood he could feel pooling in the bottom of his stomach at the thought of what he was going to do. This would top all the times he'd spent watching videos that popped up when he searched _'straight twinks jerk off together'_ or something like that.

"Get some lube first," he instructed and watched as Jack grabbed the bottle. "There you go, pour some on your hand."

Jack did as he was told, drizzling some of the slick liquid over his right hand. He closed his hands, fingers dipping into it, smearing the lube over his palm. Dean rolled his bottom lip in between his teeth as he watched.

"And now?" Jack looked at Dean expectantly.

"Now you make a circle with your hand, like this, kind of like a fist but not as tight," Dean showed him how, "and you slide your dick through your hand. Find what you like, try adding pressure, going faster or slower... "

He watched as Jack focused, tongue poking our between his lips a little as he slid his hand down over his cock. "Ohh," the boy let out a sigh, hips bucking a little. So needy for touch. Jack rubbed himself a few times, up and down, up and down, the head of his dick glistening as it got coated in lube. The length of him slid right through the hand easily, too easy.

"Wait, hold on," Dean said then and grabbed his arm. "You gotta- here, let me."

Damn kid wasn't really on a mission, had no goal in sight or emotion when he tugged on his cock. To say that it was frustrating to watch was an understatement.

Dean closed his hand over Jack's, his strong hand closing over the nephilim's easily. The feel of his soft hand relaxing under Dean's was delicious, damn he'd probably let him do whatever, trust Dean completely to do absolutely anything. Slowly, Dean began moving their hands up and down, adding pressure as he slid down all the way to the base of Jack's cock. Then up again, rolling over the head of his cock softly a few times.

"Dean," Jack moaned all breathy, eerily reminiscent of Cas. It did unspeakable things to Dean's dick and he frowned hard, turning his focus back to the task at hand.

"C'mon, you gotta pay attention."

Dean wanted to take his time, pull Jack apart slowly, piece by piece until the boy was a writhing, crying mess on his bed. But he didn't have much time. Jack was close, Dean could feel his dick pulsating in his hand, frustratingly hard as he let a thumb slip over the slit, spreading the precome collected there down over his cock, making it slide so goddamn deliciously through his fingers that his mind was threatening to go into a frenzy.

"Please," Jack mumbled, eyes closed tightly, his lube-slicked hand coming up to grab onto Dean's bicep and-- wait, when had he let go of his dick?

"I got you," Dean said quietly, his hand working faster now, pumping and twisting his wrist in rhythm with the way Jack bucked his hips as breathy moans slipped over the boy's lips.

"I- I think-"

"C'mon, c'mon you're so close baby," Dean whispered, his own mouth betraying him. He circled his hand around his cock. Fuck. It was silky smooth, and so hard, painfully so, all for Dean. It was too much, the hot and heavy weight in his hand, the slick sound of skin as Dean tugged on the cock, his needy whimpery-breaths, it was all too much.

"Ah-ah-" the hand on his bicep tightened, his fingers pressing little memories into Dean's skin, and then his cock was spurting stripes of white all over Dean's hand.

"There you go, baby, that's good, yeah, just like that." Dean closed his eyes and smeared the white down together with the rest of the mess in his hand as he continued pumping him slowly now, milking him until the last drop and his breaths had steadied somewhat.

Cas was fucking amazing.

Wait. No.

_Jack_. Jack was fucking amazing. _Fuck_.

Dean clenched his jaw and pulled his hand away from the kid. His back cracked a little as he sat up straighter, noticing he'd become kind of slumped over during their... lesson or whatever the hell this was.

"There. Next time you got a problem downstairs, do that. Yourself," Dean said, lower left arm folded over his crotch to hide his own erection.

The kid smiled that bright smile that wasn't fucking allowed anymore. Honestly. Dean needed to do something about that, later. Now, he had more pressing matters at hand.

"Wow, Dean. Thank you."

"Yeah, don't mention it."

Seriously, _don't_.

He nodded towards the tissue box. "Clean yourself up and leave me alone now, got it?"

The kid did as he was told, perfectly obedient, finally leaving Dean to take care of his own problem.

As soon as the door closed, he unzipped his pants and wasted no time, pulling his hard cock out in record time and smeared his sticky hand all over it, coming hard to the idea of bending that soft nephilim over, imagining he would be soft as butter in his hands, maybe he'd even say thank you, too.

Dean had to teach him some more, sometime. Definitely.


End file.
